The present invention relates to maltyl-2-methyl alkenoates having the structure: ##STR3## wherein R is an alkenyl moiety having one of the structures: ##STR4## and uses thereof to augment or enhance the aroma of perfume compositions, perfumed articles and colognes.
There has been considerable work performed relating to substances which can be used to augment or enhance or impart aromas to (or in) various consumable materials, such as perfume compositions, perfumed articles and colognes. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Sweet, fruity, jammy, pineapple-like, strawberry and green floral aromas and nuances are desirable in perfume compositions, perfumed articles and colognes.
U.S. Pat. No. 4,000,327 issued on Dec. 28, 1976 discloses the use in perfume compositions and perfumed articles of esters of 2-methyl-cis-3-pentenoic acid wherein the ester moiety is lower alkyl having from 2 up to 6 carbon atoms.
British Pat. No. 1,379,038 published on Jan. 2, 1975 includes a broad disclosure of .gamma.,.delta.-unsaturated carbonyl compounds, useful as flavoring and odoriferous agents of the formula: ##STR5## (where m is 0 or 1; n=0 and the dotted line is a bond or n=1 and the dotted line is no bond; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each H, or linear or branched (a) cyclic, (un)saturated univalent hydrocarbon or oxygen-substituted hydrocarbon; or R.sup.7 with R.sup.3 or R.sup.4 or R.sup.5 may form a cycloaliphatic group, provided that R.sup.3 and R.sup.5 may not contain a multiple bond which is conjugated with the alpha, beta-bond) as being prepared by reacting an alpha-beta-unsaturated carbonyl compound (R.sup.5)(R.sup.3).sub.n C.dbd.C(C)--(O).sub.m --R.sup.7 or halogenated carbonyl compound X(R.sup.5)(R.sup.3).sub.n --CH(R.sup.4).sub.n ---C(O)--R.sup.7 with an organometallic compound comprising a transition metal (preferred: Cu), an univalent cation (preferred: Li+) or [Mg-HALOGEN]+ and an alkenyl radical R.sup.6 --C(R.sup.1).dbd.C(R.sup.2)--, preferred in the presence of a complexing agent e.g. diethyl ether, tetrahydrofuran, dimethoxyethane, N-tributylphosphine or trimethylphosphite.
Maltol itself having the structure: ##STR6## is described by Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)" at number 1831 as being useful in perfumery.
However, nothing set forth in the above-mentioned prior art or in any other pertinent prior art discloses novel compounds of our invention with structures even remotely similar to the novel compounds of our invention. Furthermore, nothing in the prior art discloses the properties of the compounds of our invention that are unobvious and advantageous in the field of alkenoic acid esters.